My issue above is solved by moving a Build Phases script we had to be the last step. The error that was in the device Console when installing was MacOS error: -67030 which means errSecCSInfoPlistFailed - The Info.plist file or the signature has been modified.
We indeed had a script that modifies the plist to update the build number to the git commit count. Moving that script to be after the 'copy bundle resources' script worked to fix this issue
Svantulden
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Going to report the bug, but it's hard to reproduce so a demo project would be hard to do. Probably need to send a TSI and try to reproduce the issue a lot with some extra logging profiles for a sysDiagnose